Fungicides are compounds, of natural or synthetic origin, which act to protect and/or cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
The present disclosure relates to 3-alkyl-5-fluoro-4-imino-3,4-dihydropyrimidin-2(1H)one compounds and their use as fungicides. The compounds of the present disclosure may offer protection against ascomycetes, basidiomycetes, deuteromycetes and oomycetes.
One embodiment of the present disclosure may include compounds of Formula I:
wherein R1 is:
C1-C6 alkyl optionally substituted with 1-3 R4;
—C(═O)R5;
—C(═O)OR5;
—CH2OC(═O)R5; or
—(CHR8)nR7;
R2 is:
C1-C6 alkyl optionally substituted with 1-3 R6;
—C(═O)R7;
—C(═O)OR7; or
—(CHR8)nR7;
wherein n is an integer from 1-3;
R3 is —S(O)2R9;
R4 is independently C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C3 alkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C2-C6 alkylaminocarbonyl, hydroxyl, deuterium, or C3-C6 trialkylsilyl;
R5 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R10, or with a 5- or 6-membered saturated or unsaturated ring system, or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R10, biphenyl or naphthyl optionally substituted with 1-3 R10;R6 is independently halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C3 alkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C2-C6 alkylaminocarbonyl, hydroxyl, deuterium, or C3-C6 trialkylsilyl;R7 is H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R10, or with a 5- or 6-membered saturated or unsaturated ring system, or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R10, biphenyl or naphthyl optionally substituted with 1-3 R10;R8 is H, C1-C6 alkyl, or C1-C6 haloalkyl;R9 is C1-C6 alkyl, C1-C6 haloalkyl, amino, C1-C6 alkylamino, C2-C6 dialkylamino, a phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R10, or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R10, or with a 5-6 fused ring system, or with a 6-6 fused ring system each containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R10, biphenyl or naphthyl optionally substituted with 1-3 R10; andR10 is independently halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C6 alkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C2-C6 alkylaminocarbonyl, C2-C6 dialkylamino, hydroxy, cyano, or nitro.
In a further embodiment, R4 is independently C1-C6 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, hydroxyl, or deuterium.
In still another embodiment, R5 is C1-C6 alkyl, C1-C6 haloalkyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R10.
In yet another embodiment, R6 is independently halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, or deuterium.
In another embodiment, R7 is C1-C6 alkyl, C1-C6 haloalkyl, phenyl or benzyl wherein each of the phenyl or the benzyl may be optionally substituted with 1-3 R10.
Still, in another embodiment, R10 is independently halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, cyano, or nitro.
In yet another embodiment, R9 is phenyl optionally substituted with 1-3 R10, or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms optionally substituted with 1-3 R10. In a further embodiment, R10 is independently halogen, C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy.
In one embodiment, R1 is C1-C3 alkyl. In another embodiment, R2 is C1-C3 alkyl, —C(═O)R5, or —C(═O)OR5. In a further embodiment, R5 is C1-C3 alkyl or phenyl. In another embodiment R1 is C1-C3 alkyl.
In another embodiment, R9 is selected from the group consisting of:

In a further embodiment, R2 is C1-C3 alkyl, —C(═O)R5, or —C(═O)OR5. In another further embodiment, R5 is C1-C3 alkyl or phenyl. In still another further embodiment, R1 is C1-C3 alkyl.
Also proposed is a compound according to Formula I, wherein R1 is: C1-C6 alkyl optionally substituted with 1-3 R4;
—C(═O)R5; or
—CH2OC(═O)R5;
R2 is: C1-C6 alkyl optionally substituted with 1-3 R6; —C(═O)R7; —C(═O)OR7; or —(CHR8)nR7;
R3 is —S(O)2R9;
R4 is hydroxyl, or deuterium;
R5 is C1-C6 alkyl, or phenyl;
R6 is deuterium;
R7 is C1-C6 alkyl, or phenyl optionally substituted with 1-3 R10;
R8 is H; n is 1
R9 is C1-C6 alkyl, or a phenyl optionally substituted with 1-3 R10, or a 5- or 6-membered saturated or unsaturated ring containing 1-3 heteroatoms wherein each ring may be optionally substituted with 1-3 R10; and
R10 is independently halogen, C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, or cyano.
Also proposed is a composition for the control of a fungal pathogen, including; at least one compound of Formula I; and a phytologically acceptable carrier material, wherein said composition is effective for the control of at least one pathogenic fungus or pathogenic fungus like organism.
In a further embodiment, the pathogenic fungus or fungus like pathogen is Septoria tritici. 
Also proposed is a method for treating a plant, comprising the steps of: applying a fungicidally effective amount of at least one of the compounds of Formula 1 to at least one surface, selected from the group of surfaces consisting of: at least one portion of a plant, an area adjacent to a plant, soil in contact with a plant, solid adjacent to a plant, a seed, and agricultural equipment.
In a further embodiment, the fungicidally effective amount Formula I is applied to a surface in the range of about 0.01 g/m2 to about 0.45 g/m2 of Formula I.
Another embodiment of the present disclosure may include a fungicidal composition for the control or prevention of fungal attack comprising the compounds described below and a phytologically acceptable carrier material.
Yet another embodiment of the present disclosure may include a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of one or more of the compounds described below to at least one of the fungus, the plant, an area adjacent to the plant, and the seed adapted to produce the plant.
The term “alkyl” refers to a branched, unbranched, or cyclic carbon chain, including methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
The term “alkenyl” refers to a branched, unbranched or cyclic carbon chain containing one or more double bonds including ethenyl, propenyl, butenyl, isopropenyl, isobutenyl, cyclohexenyl, and the like.
The term “alkynyl” refers to a branched or unbranched carbon chain containing one or more triple bonds including propynyl, butynyl and the like.
As used throughout this specification, the term ‘R’ refers to the group consisting of C1-8 alkyl, C3-8 alkenyl or C3-8 alkynyl, unless stated otherwise.
The term “alkoxy” refers to an —OR substituent.
The term “alkoxycarbonyl” refers to a —C(O)—OR substituent.
The term “alkylcarbonyl” refers to a —C(O)—R substituent.
The term “alkylsulfonyl” refers to an —SO2—R substituent.
The term “alkylthio” refers to an —S—R substituent.
The term “halothio” refers to a sulfur substituted with three or five F substituents.
The term “haloalkylthio” refers to an alkylthio, which is substituted with Cl, F, I, or Br or any combination thereof.
The term “alkylaminocarbonyl” refers to a —C(O)—N(H)—R substituent.
The term “trialkylsilyl” refers to —SiR3.
The term “cyano” refers to a —C≡N substituent.
The term “hydroxyl” refers to an —OH substituent.
The term “amino” refers to a —NH2 substituent.
The term “alkylamino” refers to a —N(H)—R substituent.
The term “dialkylamino” refers to a —NR2 substituent.
The term “alkoxyalkyl” refers to an alkoxy substitution on an alkyl.
The term “halogen” or “halo” refers to one or more halogen atoms, defined as F, Cl, Br, and I.
The term “nitro” refers to a —NO2 substituent.
Unless specifically noted or clearly implied otherwise the term “about” refers to a range of values of plus or minus 10 percent, e.g. about 1 refers to the range 0.9 to 1.1.
Throughout the disclosure, reference to the compounds of Formula I is read as also including optical isomers and salts of Formula I, and hydrates thereof. Specifically, when Formula I contains a branched chain alkyl group, it is understood that such compounds include optical isomers and racemates thereof. Exemplary salts include: hydrochloride, hydrobromide, hydroiodide, and the like. Additionally, the compounds of Formula I may include tautomeric forms.
Certain compounds disclosed in this document can exist as one or more isomers. It will be appreciated by those skilled in the art that one isomer may be more active than the others. The structures disclosed in the present disclosure are drawn in only one geometric form for clarity, but are intended to represent all geometric and tautomeric forms of the molecule.
It is also understood by those skilled in the art that additional substitution is allowable, unless otherwise noted, as long as the rules of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity.
Fungicidally effective amount of the compounds include amounts sufficient to kill or control true fungi, pseudo-fungi, and related organisms including water moulds.
Another embodiment of the present disclosure is a use of a compound of Formula I, for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, comprising the application of a compound of Formula I, or a composition comprising the compound to soil, a plant, a part of a plant, foliage, and/or seeds.
Additionally, another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested by a phytopathogenic organism comprising a compound of Formula I and a phytologically acceptable carrier material.
Additional features and advantages of the present invention will become apparent to those skilled in the art upon consideration of the following detailed description of the illustrative embodiments exemplifying the best mode of carrying out the invention as presently perceived.